The present invention provides novel alkylidene alkenals useful for altering the organoleptic properties of consumable materials such as foodstuffs, tobacco products, and perfumes.
U.S. Pat. No. 3,463,818 shows unsaturated aldehydes having various floral odors and processes for preparing such compounds. Japanese published application 72/43526 shows the synthesis of terpene derivatives having orange-like odors, and hexadienal derivatives are shown. Wiemann et al, Bul. Soc. Chem. de France Memoires Presentes Soc. Chim., 1966, 1760, describe nuclear magnetic residence studies on some conjugated dienals, and a number of these compounds, including 2-ethylidene-3-pentenal are shown. 2-Propenyl-2-pentenal is mentioned in Chem. Abstracts 35, 6238.
West German published application 1,951,883 is said in Chem. Abstracts 75, 5246 to show preparation of dienals useful as perfumes. Tiffeneau et al, Comptes Rend. 204, 590 show the preparation of 2-alkylidene-3-butenal.
U.S. Pat. Nos. 3,272,873; 3,453,317; and 3,493,619 show processes for preparing unsaturated aldehydes or for treating such aldehydes. U.S. Pat. No. 3,520,936 shows production of an unsaturated aldehyde, and U.S. Patent 3,542,878 shows an aldol condensation using a tin catalyst.
Odiger et al Annalen 682 58; Corey et al, J. Am. Chem. Soc. 90, 6816; and Wittig et al, Chem. Ber. 94 676 show alkylidenation reactions utilizing phosphorus compounds. Goldberg et al shows selective reduction of unsaturated Schiff base systems in J. Am. Chem. Soc. 77, 1955.